Dean Kelly began his career at Tolka Rovers but was also a part of the 2010 Crumlin United squad that reached the third round of the FAI Cup, where the Dublin side lost 3-0 to First Division Finn Harps. However Kelly's performances led to a trial at Oldham Athletic where boss Paul Dickov was impressed enough to offer the Dubliner a sixth month contract. In his time at Boundary Park Kelly made 15 competitive appearances and scored one goal, in a 4-2 win over Plymouth Argyle.

In January 2011 Kelly was released having come to the end of his contract and signed for Michael O'Neill at Shamrock Rovers. He made his debut for Rovers against Lisburn Distillery in the Setanta Cup on March 14th, scoring one of the goals in a 3-0 win and made his league bow on the opening night of the league season as a late substitute against Dundalk at Tallaght Stadium. Dean made 11 league appearances in 2011 and scored just one league goal, though that happened to be the 94th minute winner at UCD on 25 October which secured the club's second successive League title. Dean did manage four more goals, netting once in each of the Leinster Senior Cup, the EA Sports Cup, the FAI Cup and the Setanta Cup.

In February 2012 Dean moved across the M50 to sign for Liam Buckley at St Patrick's Athletic and scored the only goal on his league debut, a 1-0 win over Bray Wanderers on the opening night of the season. He went on to make 11 league appearances but his only other goal came against Monaghan United and was scratched from the records when Monaghan withdrew from the league later that year.

In December 2012 Dean signed for Alan Mathews at Shelbourne. Dean scored nine goals in 26 league appearances for Shels, but couldn't prevent them from being relegated at the end of the season. Dean left the club after their relegation, joining up with the Fifpro squad for trial games.

Dean signed for Shamrock Rovers in February 2014. He went on to play 15 times for the Tallaght side in the league, scoring four goals which all resulted in wins. He also turned out once for the First Division B team. In December 2014, Dean signed on for Bohemians where he went on to score five goals in 16 league appearances, His most memorable performance came in the game against former club Shamrock Rovers as he came off the bench to score two goals in the 3-1 win at Dalymount Park. In July 2015, Dean moved to Longford Town under Tony Cousins and finished the season with four goals from 12 league games as the Midlands club finished sixth.

In December 2015, Dean moved to Bray Wanderers and in the 2016 campaign he netted three times from 17 league appearances.

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